endo 11 (Di­benzyl­amino)­tetra­cyclo­[5 4 0 03,10 05,9]undecane 8 one

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(1)organic compounds Acta Crystallographica Section E. Experimental. Structure Reports Online. Crystal data. ISSN 1600-5368. endo-11-(Dibenzylamino)tetracyclo[5.4.0.03,10.05,9]undecane-8-one Rajshekhar Karpoormath,a Patrick Govender,b Thavendran Govender,c Hendrik G. Krugera and Glenn E. M. Maguirea* a. School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, Department of Biochemistry, University of KwaZulu-Natal, Durban 4000, South Africa, and cSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa Correspondence e-mail: maguireg@ukzn.ac.za. C25H21NO Mr = 351.43 Monoclinic, P21 =n ˚ a = 6.6117 (3) A ˚ b = 16.4344 (7) A ˚ c = 17.2331 (8) A  = 97.100 (2). ˚3 V = 1858.18 (14) A Z=4 Cu K radiation  = 0.59 mm 1 T = 173 K 0.43  0.33  0.25 mm. Data collection Bruker Kappa DUO APEXII diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2006) Tmin = 0.786, Tmax = 0.867. 24662 measured reflections 3303 independent reflections 3240 reflections with I > 2(I) Rint = 0.018. b. Received 6 October 2010; accepted 8 February 2011 ˚; Key indicators: single-crystal X-ray study; T = 173 K; mean (C–C) = 0.004 A disorder in main residue; R factor = 0.066; wR factor = 0.173; data-to-parameter ratio = 13.0.. The structure of the title compound, C25H27NO, is a monoketone pentacycloundecane (PCU) molecule bearing a tertiary amine group. One of the methylene groups in the PCU is disordered over two orientations with site-occupancy factors of 0.621 (7) and 0.379 (7).. Related literature For mono-ketone PCU derivatives, see: Kruger et al. (2006). For examples of the crystal structures of mono-ketone PCU molecules bearing heteroatoms, see: Watson et al. (2000); Karpoormath et al. (2010).. Refinement R[F 2 > 2(F 2)] = 0.066 wR(F 2) = 0.173 S = 1.06 3303 reflections 255 parameters. 24 restraints H-atom parameters constrained ˚ 3 max = 0.48 e A ˚ 3 min = 0.46 e A. Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.. The authors would like to thank Dr Hong Su from the University of Capetown for the data collection and structure refinement. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2177).. References Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. Bruker (2006). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Karpoormath, R., Govender, T., Govender, P., Kruger, H. G. & Maguire, G. E. M. (2010). Acta Cryst. E66, o2607–o2608. Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268– o270. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Watson, W. H., Bodige, S. G., Marchand, A. P. & Chong, H.-S. (2000). Struct. Chem. 11, 257–260.. Acta Cryst. (2011). E67, o619. doi:10.1107/S160053681100479X. Karpoormath et al.. o619.

(2) supporting information. supporting information Acta Cryst. (2011). E67, o619. [doi:10.1107/S160053681100479X]. endo-11-(Dibenzylamino)tetracyclo[5.4.0.03,10.05,9]undecane-8-one Rajshekhar Karpoormath, Patrick Govender, Thavendran Govender, Hendrik G. Kruger and Glenn E. M. Maguire S1. Comment We have reported the structures of a number of PCU derivatives including a mono-ketone ethylene acetal (Kruger et al., 2006). We more recently reported the structure of a mono–ketone pentacycloundecane (PCU) (Karpoormath et al. 2010), that demonstrated intramolecular hydrogen bonding, a quite uncommon feature hitherto in mono–ketone PCU structures (Watson et al., 2000). In that example the racemate occupied alternative sites in the unit cell. Herein, we report the crystal structure of the title compound (Fig. 1). The C1 methylene group in PCU is disordered over two positions with site–occupancy factors of 0.621 (7) (for atom labelled A) and 0.379 (7) (for atom labelled B) in Fig. 1. S2. Experimental A solution of PCU cage N-dibenzyl mono ethylene ketal (0.5 g, 1.25 mmol) in 10 ml of THF was stirred at room temperature for 5 minutes. To this mixture was added 10 ml of 10% HCL solution and stirred overnight at room temperature. THF was removed from the crude product under vacuum using a teflon pump at 80 °C to obtain an aqueous solution with white precipitate. The precipitate was collected by vacuum filtration and washed with water (50 ml) to give a white solid. The yield was 97%. Crystallization of the title compound was carried out by dissolving the compound in ethyl acetate and hexane (1:4) with storage at 20 °C. Melting point: 438–439 K. IR (neat) Vmax cm-1: 3376.61, 2978.73, 2961.26, 2794.11, 1721.74, 1602.42, 1494.57, 1342.20, 1131.34, 752.25, 731.39, 696.73, cm-1. 1H NMR (CDCl3, 400 MHz) δ p.p.m.: 1.56 (1.0H, d, J=11.13 Hz), 1.89 (1.0H, d, J=11.13 Hz), 2.52 (1.0H, d, J=4.56 Hz), 2.61 (1.0H, d, J=6.96 Hz), 2.71 (2.0H, d, J=5.96 Hz), 2.90 (1.0H, d, J=5.60 Hz), 2.93 (1.0H, d, J=4.68 Hz), 3.50 (1.0H, d, J=2.28 Hz), 3.51 (2.0H, t, J=12.27 Hz), 3.90 (1.0H, t, J=5.02 Hz), 4.39 (1.0H, d, J=14.65 Hz), 4.52 (2.0H, dd, J=9.87, 14.55 Hz), 4.81 (1.0H, d, J=14.61 Hz), 6.90 (2.0H, d, J=7.24 Hz), 6.99 (2.0H, d, J=7.20 Hz), 7.23 - 7.38 (6.0H, m, J=7.20 Hz). 13C NMR (CDCl3, 101 MHz) δ p.p.m.: 40.75 (d, J=15.71 Hz), 41.28 (d, J=14.29 Hz), 43.15 (s), 44.18 (s), 46.12 (s), 50.09 (s), 52.72 (s), 59.20 (d, J=73.03 Hz), 70.28 (s), 123.86 (s), 129.41 (d, J=10.10 Hz), 129.92 (s), 130.45 (d, J=24.83 Hz), 131.13 (s). HR ESI m/z: calcd for C25H25NO [M+H]+:356.2009 found 356.2014. S3. Refinement All hydrogen atoms were positioned geometrically with C—H = 0.95–1.00 Å and refined as riding on their parent atoms, with Uiso (H) = 1.2 Ueq (C). The C1 methylene group was found to be disordered over two positions and modelled with site–occupancy factors, from refinement of 0.621 (7) (C1A) and 0.379 (7) (C1B), respectively. The distance of C2—C1A, C6—C1B and C7—C1A and C11—C1B sets were restrained to 0.001 Å using command SADI and DELU. The displacement ellipsoids of C1A and C1B were restrained using commend ISOR (0.01).. Acta Cryst. (2011). E67, o619. sup-1.

(3) supporting information. Figure 1 The molecular structure of the title compound with atomic numbering scheme. All hydrogen atoms are omitted for clarity. Displacement ellipsoids are drawn at the 25% probability level. The C1 methylene group was found to be disordered over two positions and modelled with site–occupancy factors, from refinement of 0.621 (7) (C1A) and 0.379 (7) (C1B). endo-11-(Dibenzylamino)tetracyclo[5.4.0.03,10.05,9]undecane-8-one Crystal data C25H21NO Mr = 351.43 Monoclinic, P21/n Hall symbol: -P 2yn a = 6.6117 (3) Å b = 16.4344 (7) Å Acta Cryst. (2011). E67, o619. c = 17.2331 (8) Å β = 97.100 (2)° V = 1858.18 (14) Å3 Z=4 F(000) = 744 Dx = 1.256 Mg m−3. sup-2.

(4) supporting information Cu Kα radiation, λ = 1.54184 Å Cell parameters from 3299 reflections θ = 5.2–69.2° µ = 0.59 mm−1. T = 173 K Needle, colourless 0.43 × 0.33 × 0.25 mm. Data collection Bruker Kappa DUO APEXII diffractometer Radiation source: fine-focus sealed tube Graphite monochromator 1.2° φ scans and ω Absorption correction: multi-scan (SADABS; Bruker, 2006) Tmin = 0.786, Tmax = 0.867. 24662 measured reflections 3303 independent reflections 3240 reflections with I > 2σ(I) Rint = 0.018 θmax = 69.2°, θmin = 3.7° h = −7→7 k = −19→19 l = −20→20. Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.066 wR(F2) = 0.173 S = 1.06 3303 reflections 255 parameters 24 restraints Primary atom site location: structure-invariant direct methods. Secondary atom site location: difference Fourier map Hydrogen site location: difference Fourier map H-atom parameters constrained w = 1/[σ2(Fo2) + (0.080P)2 + 1.983P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.48 e Å−3 Δρmin = −0.46 e Å−3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0020 (4). Special details Experimental. Half sphere of data collected using APEX2 (Bruker, 2006). Crystal to detector distance = 45 mm; combination of φ and ω scans of 1.2°, 50 s per °, 2 iterations. Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2). O1 N1 C2 C3 H3 C4 H4 C5 H5. x. y. z. Uiso*/Ueq. 0.1742 (2) −0.2672 (3) −0.4175 (5) −0.3558 (3) −0.4438 −0.3624 (3) −0.5077 −0.2577 (4) −0.2759. 0.13889 (10) 0.05165 (10) 0.27147 (16) 0.19546 (14) 0.1857 0.12730 (13) 0.1160 0.16781 (17) 0.1387. 0.19402 (10) 0.14408 (10) 0.1215 (3) 0.17218 (17) 0.2145 0.11264 (14) 0.0920 0.04842 (17) −0.0029. 0.0394 (4) 0.0271 (4) 0.0763 (12) 0.0423 (6) 0.051* 0.0347 (5) 0.042* 0.0493 (7) 0.059*. Acta Cryst. (2011). E67, o619. Occ. (<1). sup-3.

(5) supporting information C6 C7 C8 H8 C9 C10 H10 C11 C12 H12A H12B C13 C14 H14 C15 H15 C16 H16 C17 H17 C18 H18 C19 H19A H19B C20 C21 H21 C22 H22 C23 H23 C24 H24 C25 H25 C1A H1A H1B C1B H1D H1C. −0.3393 (6) −0.1306 (5) −0.1293 (3) −0.0991 0.0227 (3) −0.0309 (4) 0.0730 −0.0792 (5) −0.3867 (3) −0.3795 −0.5311 −0.3230 (3) −0.4688 (4) −0.6085 −0.4127 (4) −0.5139 −0.2108 (4) −0.1722 −0.0654 (4) 0.0736 −0.1200 (4) −0.0184 −0.2474 (4) −0.1791 −0.3851 −0.1277 (3) 0.0737 (3) 0.1342 0.1864 (4) 0.3238 0.1013 (4) 0.1796 −0.0992 (4) −0.1593 −0.2121 (4) −0.3498 −0.3205 (6) −0.3673 −0.3281 −0.2299 (8) −0.2791 −0.2020. 0.25559 (17) 0.30438 (16) 0.22060 (14) 0.2233 0.17342 (14) 0.19225 (18) 0.1760 0.2836 (2) 0.01601 (13) −0.0440 0.0318 0.03943 (13) 0.04214 (14) 0.0347 0.05563 (15) 0.0568 0.06739 (16) 0.0761 0.06631 (17) 0.0755 0.05196 (15) 0.0507 −0.00746 (14) 0.0190 −0.0244 −0.08185 (13) −0.07388 (14) −0.0214 −0.14184 (16) −0.1357 −0.21862 (15) −0.2652 −0.22698 (15) −0.2795 −0.15900 (14) −0.1653 0.3417 (2) 0.3612 0.3860 0.3246 (3) 0.3753 0.3321. 0.04539 (18) 0.16140 (19) 0.20361 (17) 0.2619 0.16393 (15) 0.07827 (17) 0.0437 0.0801 (2) 0.20230 (13) 0.1982 0.1884 0.28639 (13) 0.33779 (14) 0.3185 0.41683 (15) 0.4514 0.44562 (15) 0.4999 0.39452 (15) 0.4138 0.31545 (14) 0.2810 0.08166 (13) 0.0403 0.0580 0.11058 (12) 0.14401 (14) 0.1496 0.16920 (16) 0.1921 0.16137 (15) 0.1785 0.12834 (15) 0.1228 0.10333 (14) 0.0808 0.1498 (2) 0.1989 0.1106 0.0321 (4) 0.0546 −0.0225. 0.0652 (10) 0.0612 (9) 0.0422 (6) 0.051* 0.0361 (5) 0.0497 (7) 0.060* 0.0775 (12) 0.0311 (5) 0.037* 0.037* 0.0307 (5) 0.0372 (5) 0.045* 0.0436 (6) 0.052* 0.0467 (6) 0.056* 0.0452 (6) 0.054* 0.0384 (6) 0.046* 0.0349 (5) 0.042* 0.042* 0.0312 (5) 0.0381 (5) 0.046* 0.0434 (6) 0.052* 0.0416 (6) 0.050* 0.0413 (6) 0.050* 0.0363 (5) 0.044* 0.0414 (11) 0.050* 0.050* 0.0458 (19) 0.055* 0.055*. 0.621 (7) 0.621 (7) 0.621 (7) 0.379 (7) 0.379 (7) 0.379 (7). Atomic displacement parameters (Å2). O1 N1. U11. U22. U33. U12. U13. U23. 0.0224 (8) 0.0261 (9). 0.0389 (9) 0.0239 (9). 0.0564 (10) 0.0310 (9). 0.0003 (6) 0.0000 (7). 0.0031 (7) 0.0019 (7). 0.0051 (7) 0.0019 (7). Acta Cryst. (2011). E67, o619. sup-4.

(6) supporting information C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C1A C1B. 0.0606 (19) 0.0238 (11) 0.0248 (10) 0.0439 (14) 0.092 (2) 0.0715 (19) 0.0278 (12) 0.0243 (11) 0.0382 (13) 0.066 (2) 0.0262 (10) 0.0311 (11) 0.0361 (12) 0.0570 (16) 0.0684 (18) 0.0445 (14) 0.0327 (12) 0.0376 (12) 0.0345 (11) 0.0333 (12) 0.0316 (12) 0.0460 (14) 0.0497 (14) 0.0351 (12) 0.052 (2) 0.062 (4). 0.0306 (14) 0.0256 (12) 0.0278 (11) 0.0489 (16) 0.0341 (14) 0.0268 (13) 0.0284 (12) 0.0292 (11) 0.0525 (16) 0.059 (2) 0.0269 (11) 0.0240 (10) 0.0309 (12) 0.0351 (13) 0.0373 (13) 0.0483 (15) 0.0435 (14) 0.0351 (12) 0.0303 (11) 0.0302 (12) 0.0429 (14) 0.0342 (13) 0.0287 (12) 0.0348 (12) 0.0290 (19) 0.031 (3). 0.148 (3) 0.0770 (18) 0.0495 (13) 0.0522 (15) 0.0589 (17) 0.075 (2) 0.0699 (17) 0.0549 (14) 0.0595 (16) 0.117 (3) 0.0404 (12) 0.0378 (12) 0.0464 (13) 0.0423 (13) 0.0338 (12) 0.0405 (13) 0.0391 (13) 0.0301 (11) 0.0287 (10) 0.0498 (14) 0.0542 (15) 0.0459 (14) 0.0467 (14) 0.0384 (12) 0.043 (2) 0.046 (3). 0.0175 (13) 0.0021 (9) 0.0006 (8) −0.0049 (12) −0.0159 (15) 0.0005 (12) −0.0016 (9) −0.0052 (9) −0.0045 (11) 0.0220 (16) −0.0041 (8) 0.0013 (8) 0.0036 (9) 0.0077 (11) 0.0072 (12) 0.0008 (11) 0.0013 (10) 0.0035 (9) 0.0012 (9) −0.0017 (9) 0.0035 (10) 0.0110 (10) −0.0026 (10) −0.0025 (9) 0.0039 (16) 0.002 (3). 0.055 (2) 0.0049 (11) −0.0037 (9) −0.0061 (12) −0.0342 (16) −0.0338 (16) 0.0041 (11) 0.0055 (10) 0.0098 (12) 0.050 (2) 0.0055 (9) 0.0069 (9) 0.0124 (10) 0.0206 (12) 0.0040 (12) −0.0041 (11) 0.0053 (10) −0.0027 (9) 0.0032 (9) 0.0011 (10) −0.0005 (11) 0.0104 (11) 0.0111 (11) 0.0020 (9) 0.0042 (17) 0.013 (3). 0.0285 (18) −0.0047 (11) 0.0082 (10) 0.0247 (12) 0.0170 (13) −0.0049 (13) −0.0090 (11) 0.0056 (10) 0.0249 (13) 0.052 (2) 0.0009 (9) 0.0060 (9) 0.0049 (10) 0.0067 (10) 0.0047 (10) 0.0043 (11) 0.0051 (10) −0.0024 (9) −0.0043 (9) −0.0011 (10) 0.0025 (11) 0.0051 (10) −0.0053 (10) −0.0085 (10) 0.0013 (15) 0.005 (3). Geometric parameters (Å, º) O1—C9 N1—C4 N1—C19 N1—C12 C2—C1A C2—C6 C2—C3 C3—C4 C3—C8 C3—H3 C4—C5 C4—H4 C5—C6 C5—C10 C5—H5 C6—C1B C7—C1A C7—C11 C7—C8. Acta Cryst. (2011). E67, o619. 1.211 (3) 1.467 (3) 1.467 (3) 1.473 (3) 1.380 (4) 1.491 (5) 1.550 (4) 1.516 (3) 1.583 (3) 1.0000 1.529 (3) 1.0000 1.539 (4) 1.576 (4) 1.0000 1.379 (4) 1.389 (4) 1.522 (5) 1.557 (4). C13—C14 C14—C15 C14—H14 C15—C16 C15—H15 C16—C17 C16—H16 C17—C18 C17—H17 C18—H18 C19—C20 C19—H19A C19—H19B C20—C25 C20—C21 C21—C22 C21—H21 C22—C23 C22—H22. 1.388 (3) 1.385 (4) 0.9500 1.379 (4) 0.9500 1.382 (4) 0.9500 1.386 (4) 0.9500 0.9500 1.507 (3) 0.9900 0.9900 1.385 (3) 1.390 (3) 1.383 (3) 0.9500 1.381 (4) 0.9500. sup-5.

(7) supporting information C8—C9 C8—H8 C9—C10 C10—C11 C10—H10 C11—C1B C12—C13 C12—H12A C12—H12B C13—C18. 1.500 (3) 1.0000 1.507 (4) 1.536 (4) 1.0000 1.387 (4) 1.508 (3) 0.9900 0.9900 1.388 (3). C23—C24 C23—H23 C24—C25 C24—H24 C25—H25 C1A—H1A C1A—H1B C1B—H1D C1B—H1C. 1.383 (4) 0.9500 1.383 (3) 0.9500 0.9500 0.9900 0.9900 0.9900 0.9900. C4—N1—C19 C4—N1—C12 C19—N1—C12 C1A—C2—C6 C1A—C2—C3 C6—C2—C3 C4—C3—C2 C4—C3—C8 C2—C3—C8 C4—C3—H3 C2—C3—H3 C8—C3—H3 N1—C4—C3 N1—C4—C5 C3—C4—C5 N1—C4—H4 C3—C4—H4 C5—C4—H4 C4—C5—C6 C4—C5—C10 C6—C5—C10 C4—C5—H5 C6—C5—H5 C10—C5—H5 C1B—C6—C2 C1B—C6—C5 C2—C6—C5 C1A—C7—C11 C1A—C7—C8 C11—C7—C8 C9—C8—C7 C9—C8—C3 C7—C8—C3 C9—C8—H8 C7—C8—H8 C3—C8—H8 O1—C9—C8. 111.32 (17) 110.30 (16) 109.88 (17) 105.1 (3) 113.4 (3) 105.0 (2) 103.3 (2) 111.81 (19) 98.9 (2) 113.8 113.8 113.8 113.65 (19) 115.1 (2) 101.0 (2) 108.9 108.9 108.9 104.2 (2) 111.9 (2) 95.0 (2) 114.6 114.6 114.6 104.3 (4) 126.0 (4) 107.0 (2) 105.5 (3) 114.2 (3) 104.1 (2) 102.1 (2) 111.6 (2) 96.9 (2) 114.7 114.7 114.7 127.8 (2). C18—C13—C14 C18—C13—C12 C14—C13—C12 C15—C14—C13 C15—C14—H14 C13—C14—H14 C16—C15—C14 C16—C15—H15 C14—C15—H15 C15—C16—C17 C15—C16—H16 C17—C16—H16 C16—C17—C18 C16—C17—H17 C18—C17—H17 C17—C18—C13 C17—C18—H18 C13—C18—H18 N1—C19—C20 N1—C19—H19A C20—C19—H19A N1—C19—H19B C20—C19—H19B H19A—C19—H19B C25—C20—C21 C25—C20—C19 C21—C20—C19 C22—C21—C20 C22—C21—H21 C20—C21—H21 C23—C22—C21 C23—C22—H22 C21—C22—H22 C22—C23—C24 C22—C23—H23 C24—C23—H23 C25—C24—C23. 118.8 (2) 121.8 (2) 119.2 (2) 120.7 (2) 119.7 119.7 120.4 (2) 119.8 119.8 119.2 (2) 120.4 120.4 120.8 (2) 119.6 119.6 120.2 (2) 119.9 119.9 112.67 (17) 109.1 109.1 109.1 109.1 107.8 118.6 (2) 121.6 (2) 119.8 (2) 120.4 (2) 119.8 119.8 120.6 (2) 119.7 119.7 119.3 (2) 120.4 120.4 120.1 (2). Acta Cryst. (2011). E67, o619. sup-6.

(8) supporting information O1—C9—C10 C8—C9—C10 C9—C10—C11 C9—C10—C5 C11—C10—C5 C9—C10—H10 C11—C10—H10 C5—C10—H10 C1B—C11—C7 C1B—C11—C10 C7—C11—C10 N1—C12—C13 N1—C12—H12A C13—C12—H12A N1—C12—H12B C13—C12—H12B H12A—C12—H12B. 126.7 (2) 104.5 (2) 101.8 (3) 111.5 (2) 93.7 (2) 115.7 115.7 115.7 102.3 (4) 126.7 (4) 108.0 (2) 116.31 (17) 108.2 108.2 108.2 108.2 107.4. C25—C24—H24 C23—C24—H24 C24—C25—C20 C24—C25—H25 C20—C25—H25 C2—C1A—C7 C2—C1A—H1A C7—C1A—H1A C2—C1A—H1B C7—C1A—H1B H1A—C1A—H1B C6—C1B—C11 C6—C1B—H1D C11—C1B—H1D C6—C1B—H1C C11—C1B—H1C H1D—C1B—H1C. 120.0 120.0 121.0 (2) 119.5 119.5 93.1 (3) 113.1 113.1 113.1 113.1 110.5 81.7 (3) 115.0 115.0 115.0 115.0 112.1. C1A—C2—C3—C4 C6—C2—C3—C4 C1A—C2—C3—C8 C6—C2—C3—C8 C19—N1—C4—C3 C12—N1—C4—C3 C19—N1—C4—C5 C12—N1—C4—C5 C2—C3—C4—N1 C8—C3—C4—N1 C2—C3—C4—C5 C8—C3—C4—C5 N1—C4—C5—C6 C3—C4—C5—C6 N1—C4—C5—C10 C3—C4—C5—C10 C1A—C2—C6—C1B C3—C2—C6—C1B C1A—C2—C6—C5 C3—C2—C6—C5 C4—C5—C6—C1B C10—C5—C6—C1B C4—C5—C6—C2 C10—C5—C6—C2 C1A—C7—C8—C9 C11—C7—C8—C9 C1A—C7—C8—C3 C11—C7—C8—C3 C4—C3—C8—C9 C2—C3—C8—C9. −145.8 (3) −31.6 (3) −30.7 (3) 83.4 (3) −170.57 (19) 67.2 (2) −54.8 (3) −177.03 (19) 167.47 (19) 62.0 (3) 43.6 (2) −61.8 (2) −162.24 (19) −39.4 (2) −60.8 (3) 62.1 (3) −8.8 (3) −128.7 (3) 126.6 (3) 6.7 (3) 143.1 (4) 29.1 (5) 20.3 (3) −93.7 (3) 144.0 (3) 29.5 (3) 30.1 (3) −84.4 (2) 2.7 (3) −105.6 (3). C4—C5—C10—C11 C6—C5—C10—C11 C1A—C7—C11—C1B C8—C7—C11—C1B C1A—C7—C11—C10 C8—C7—C11—C10 C9—C10—C11—C1B C5—C10—C11—C1B C9—C10—C11—C7 C5—C10—C11—C7 C4—N1—C12—C13 C19—N1—C12—C13 N1—C12—C13—C18 N1—C12—C13—C14 C18—C13—C14—C15 C12—C13—C14—C15 C13—C14—C15—C16 C14—C15—C16—C17 C15—C16—C17—C18 C16—C17—C18—C13 C14—C13—C18—C17 C12—C13—C18—C17 C4—N1—C19—C20 C12—N1—C19—C20 N1—C19—C20—C25 N1—C19—C20—C21 C25—C20—C21—C22 C19—C20—C21—C22 C20—C21—C22—C23 C21—C22—C23—C24. −107.2 (3) 0.3 (3) 10.1 (3) 130.7 (3) −125.5 (3) −4.9 (3) −142.8 (4) −29.9 (5) −21.3 (3) 91.6 (3) −92.8 (2) 144.12 (18) −35.2 (3) 150.2 (2) −1.1 (3) 173.7 (2) 0.6 (4) 0.6 (4) −1.3 (4) 0.8 (4) 0.4 (4) −174.3 (2) 173.10 (18) −64.4 (2) 120.5 (2) −60.8 (3) 0.1 (4) −178.6 (2) 0.2 (4) −0.4 (4). Acta Cryst. (2011). E67, o619. sup-7.

(9) supporting information C4—C3—C8—C7 C2—C3—C8—C7 C7—C8—C9—O1 C3—C8—C9—O1 C7—C8—C9—C10 C3—C8—C9—C10 O1—C9—C10—C11 C8—C9—C10—C11 O1—C9—C10—C5 C8—C9—C10—C5 C4—C5—C10—C9 C6—C5—C10—C9. Acta Cryst. (2011). E67, o619. 108.6 (2) 0.3 (3) 124.9 (3) −132.5 (3) −44.2 (2) 58.4 (3) −128.6 (3) 40.7 (2) 132.6 (3) −58.1 (3) −2.9 (3) 104.5 (3). C22—C23—C24—C25 C23—C24—C25—C20 C21—C20—C25—C24 C19—C20—C25—C24 C6—C2—C1A—C7 C3—C2—C1A—C7 C11—C7—C1A—C2 C8—C7—C1A—C2 C2—C6—C1B—C11 C5—C6—C1B—C11 C7—C11—C1B—C6 C10—C11—C1B—C6. 0.2 (4) 0.1 (4) −0.3 (3) 178.4 (2) −67.4 (3) 46.7 (4) 66.7 (3) −46.9 (4) 83.9 (4) −40.0 (5) −82.9 (4) 40.9 (5). sup-8.

(10)

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